Substituted heteroaryl derivatives

Abstract

The invention relates to substituted heteroaryl derivatives, to methods for the production thereof, to medicaments containing said compounds and to the use of substituted heteroaryl derivatives for producing medicaments.

The invention claimed is: 
     
       1. Substituted heteroaryl derivatives of the formula I 
       
         
           
           
               
               
           
         
         wherein 
         A represents N or CR 7-10 , wherein A represents N at most twice 
         W represents O, S or NR 4    
         with the proviso that if W represents O or S, A denotes CR 7-10 ; 
         one of the radicals B or C represents H; C 1-8 -alkyl, in each case saturated or unsaturated, branched or unbranched, mono- or polysubstituted or unsubstituted, COR 12 ; SO 2 R 12 ; aryl, C 3-8 -cycloalkyl or heteroaryl bonded via C 1-3 -alkyl and in each case mono- or polysubstituted or unsubstituted, aryl or heteroaryl, in each case mono- or polysubstituted or unsubstituted; C 3-8 -cycloalkyl, in each case mono- or polysubstituted or unsubstituted; and the other particular radical B or C represents 
       
       
         
           
           
               
               
           
         
         wherein 
            represents a single bond or a double bond, 
         R 1  and R 2  independently of one another represent H; C 1-5 -alkyl, in each case saturated or unsaturated, branched or unbranched, mono- or polysubstituted or unsubstituted, except that neither R 1  nor R 2  may represent alkyl substituted by unsubstituted or substituted O-phenyl; C 3-8 -cycloalkyl, in each case mono- or polysubstituted or unsubstituted; aryl or heteroaryl, in each case mono- or polysubstituted or unsubstituted; or aryl, C 3-8 -cycloalkyl or heteroaryl, bonded via C 1-3 -alkyl and in each case mono- or polysubstituted or unsubstituted; 
         or the radicals R 1  and R 2  together represent CH 2 CH 2 OCH 2 CH 2 , CH 2 CH 2 NR 11 CH 2 CH 2  or (CH 2 ) 3-6 ,
 wherein R 11  denotes H; C 1-5 -alkyl, in each case saturated or unsaturated, branched or unbranched, mono- or polysubstituted or unsubstituted; C 3-8 -cycloalkyl, in each case mono- or polysubstituted or unsubstituted; aryl or heteroaryl, in each case mono- or polysubstituted or unsubstituted; or aryl, C 3-8 -cycloalkyl or heteroaryl, bonded via C 1-3 -alkyl and in each case mono- or polysubstituted or unsubstituted; C(O)phenyl, C(O)heteroaryl, C(O)C 1-5 -alkyl, in each case substituted or unsubstituted; 
 
       
       and 
       R 3  represents C 1-8 -alkyl, in each case saturated or unsaturated, branched or unbranched, mono- or polysubstituted or unsubstituted; C 3-8 -cycloalkyl, in each case mono- or polysubstituted or unsubstituted; aryl or heteroaryl, in each case unsubstituted or mono- or polysubstituted; aryl, heteroaryl or C 3-8 -cycloalkyl, bonded via C 1-3 -alkyl group and in each case unsubstituted or mono- or polysubstituted; 
       R 4  represents H; C 1-5 -alkyl, saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted; aryl, or heteroaryl, in each case substituted or unsubstituted; aryl, heteroaryl or cycloalkyl, bonded via a C 1-3 -alkyl group and in each case mono- or polysubstituted or unsubstituted; COR 12 ; SO 2 R 12 ,
 wherein R 12  denotes H; C 1-5 -alkyl, in each case saturated or unsaturated, branched or unbranched, mono- or polysubstituted or unsubstituted; C 3-8 -cycloalkyl, in each case saturated or unsaturated, mono- or polysubstituted or unsubstituted; aryl or heteroaryl, in each case mono- or polysubstituted or unsubstituted; or aryl, C 3-8 -cycloalkyl or heteroaryl, bonded via C 1-3 -alkyl and in each case mono- or polysubstituted or unsubstituted; OR 13 ; NR 14 R 15 ; 
 
       R 7 , R 8 , R 9  and R 10  independently of one another represent 
       H, F, Cl, Br, I, NO 2 , CF 3 , OR 13 , SR 13 , SO 2 R 13 , SO 2 OR 13 , CN, COOR 13 , NR 14 R 15 , NHC(O)NHR 13 , NHC(O)R 13 , NH(CNR 13 )NHR 13 , SO 2 NHR 13 ; C 1-5 -alkyl, C 3-8 -cycloalkyl, unsubstituted or mono- or polysubstituted; aryl or heteroaryl, unsubstituted or mono- or polysubstituted; or aryl, C 3-8 -cycloalkyl or heteroaryl, bonded via C 1-3 -alkyl and unsubstituted or mono- or polysubstituted;
 wherein R 13  denotes H; C 1-5 -alkyl, in each case saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted; C 3-8 -cycloalkyl, in each case saturated or unsaturated, unsubstituted or mono- or polysubstituted; aryl or heteroaryl, unsubstituted or mono- or polysubstituted; or aryl, C 3-8 -cycloalkyl or heteroaryl, bonded via C 1-3 -alkyl and unsubstituted or mono- or polysubstituted; 
 
       or R 7 , R 8  and R 9  have the abovementioned meaning and R 10  together with B represents —CH 2 CH 2 CH 2 — and R 10  and B therefore form a six-membered ring, 
       R 14  and R 15  independently of one another denote H; C 1-5 -alkyl, in each case saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted; or C 3-8 -cycloalkyl, in each case saturated or unsaturated, unsubstituted or mono- or polysubstituted; aryl or heteroaryl, unsubstituted or mono- or polysubstituted; or aryl, C 3-8 -cycloalkyl or heteroaryl, bonded via C 1-3 -alkyl and unsubstituted or mono- or polysubstituted; 
       or R 14  and R 15  together form CH 2 CH 2 OCH 2 CH 2 , CH 2 CH 2 NR 16 CH 2 CH 2  or (CH 2 ) 3-6 ,
 wherein R 16  denotes H; C 1-5 -alkyl, saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted; 
 in the form of the racemate; of the enantiomers, diastereomers, mixtures of the enantiomers or diastereomers or of an individual enantiomer or diastereomer; of the bases and/or salts of physiologically acceptable acids. 
 
     
     
       2. Substituted heteroaryl derivatives according to  claim 1 , wherein
 the C 1-8 -alkyls, C 1-5 -alkyls, C 1-3 -alkyls or C 1-3 -alkylenes or C 3-8 -cycloalkyl radicals can in each case be mono- or polysubstituted by F, Cl, Br, I, —CN, NH 2 , NH—C 1-6 -alkyl, NH—C 1-6 -alkyl-OH, N(C 1-6 -alkyl) 2 , N(C 1-6 -alkyl-OH) 2 , NO 2 , SH, S—C 1-6 -alkyl, S-benzyl, OCF 3 , O—C 1-6 -alkyl, OH, O—C 1-6 -alkyl-OH, ═O, 
 C 1-6 -alkyl, benzyl, O-benzyl, O-phenyl, C(═O)C 1-6 -alkyl, CO 2 H, NHC(═O)C 1-6 -alkyl, OC(═O)C 1-6 -alkyl, CO 2 —C 1-6 -alkyl, 
 the aryl or heteroaryl radicals can in each case be mono- or polysubstituted by F, Cl, Br, I, CN, NH 2 , NH—C 1-6 -alkyl, NH—C 1-6 -alkyl-OH, 
 N(C 1-6 alkyl) 2 , N(C 1-6 -alkyl-OH) 2 , NO 2 , SH, S—C 1-6 -alkyl, OH, O—C 1-6 -alkyl, O—C 1-6 alkyl-OH, C(═O)C 1-6 -alkyl, CO 2 H, CO 2 —C 1-6 -alkyl, CF 3 , OCF 3 , C 1-6 -alkyl or phenoxy, 
 in the form of the racemate; of the enantiomers, diastereomers, mixtures of the enantiomers or diastereomers or of an individual enantiomer or diastereomer; of the bases and/or salts of physiologically acceptable acids. 
 
     
     
       3. Heteroaryl derivatives according to  claim 1 , wherein
 R 1  and R 2  independently of one another represent H; C 1-5 -alkyl, saturated or unsaturated, branched or unbranched, mono- or polysubstituted or unsubstituted; 
 or the radicals R 1  and R 2  together form a ring and denote CH 2 CH 2 OCH 2 CH 2 , CH 2 CH 2 NR 11 CH 2 CH 2  or (CH 2 ) 3-6 , 
 wherein R 11  denotes H; C 1-5 -alkyl, saturated or unsaturated, branched or unbranched, mono- or polysubstituted or unsubstituted. 
 
     
     
       4. Heteroaryl derivatives according to  claim 3 , wherein R 1  and R 2  independently of one another represent CH 3  or H, wherein R 1  and R 2  do not simultaneously denote H. 
     
     
       5. Substituted heteroaryl derivatives according to  claim 1 , wherein R 3  denotes butyl, phenyl, thiophenyl, thiazolyl, cyclopentyl, cyclohexyl, naphthyl, benzyl, benzofuranyl, 1,2,4-triazolyl, benzimidazolyl, benzodioxanyl, benzodioxolanyl, pyridyl or benzothiophenyl, in each case unsubstituted or mono- or polysubstituted; phenyl, furyl or thiophenyl bonded via a saturated, unbranched C 1-3 -alkyl group and in each case unsubstituted or mono- or polysubstituted. 
     
     
       6. Substituted heteroaryl derivatives according to  claim 5 , wherein R 3  denotes phenyl, 4-fluorophenyl, benzyl, butyl or benzothiophenyl. 
     
     
       7. Substituted heteroaryl derivatives according to  claim 1 , wherein B or C represents (CH 2 ) 1-4 —R 21 , wherein R 21  represents H, OH, SH, COOC 1-6 -alkyl, COOH, OC(═O)C 1-6 -alkyl, NH 2 , NHC(═O)C 1-6 -alkyl; or C 3-8 -cycloalkyl, aryl or heteroaryl, in each case unsubstituted or mono- or polysubstituted. 
     
     
       8. Substituted heteroaryl derivatives according to  claim 7 , wherein R 21  represents OH, SH, COOCH 3 , COOH, OC(═O)CH 3 , NH 2 , NHC(═O)CH 3 , NHC(═O)CH 2 C(CH 3 ) 2 ; or benzimidazole, pyridyl, triazolyl, phenyl, pyrazolyl, tetrazolyl or imidazolyl, in each case unsubstituted or substituted by COOCH 3 , CH 3 ; or cyclopropyl, cyclohexyl, pyrrolidinyl tetrahydroquinolinyl, pyrrolidinyl, piperidyl, tetrahydroisoquinolinyl, isoindolinyl, piperazinyl, morpholinyl or thiazolinyl, in each case unsubstituted or substituted by ═O or CH 3 . 
     
     
       9. Substituted heteroaryl derivatives according to  claim 1 , wherein R 7 , R 8 , R 9  and R 10  independently of one another represent H; methyl; ethyl; propyl; butyl; pyridyl, O-benzyl, F, Cl, Br, I, CN, CF 3 , OCF 3 , OH, OCH 3 , NH 2 , COOH, COOCH 3 , NHCH 3  or N(CH 3 ) 2  or NO 2 . 
     
     
       10. Substituted heteroaryl derivatives according to  claim 9 , wherein R 7 , R 8 , R 9  and R 10  independently of one another represent H, F, Cl, NO 2 , CN, CF 3 , OCH 3 , OCF 3  or OH. 
     
     
       11. Substituted heteroaryl derivatives according to  claim 1 , which are selected from the group consisting of:
 (1) 2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethanol, citrate; 
 (3) (±) 2-(2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-1H-indol-3-yl)ethyl acetate hydrochloride; 
 (4) (±) 2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-3-(3-aminopropyl)-1H-indole, citrate; 
 (6) (±) 3-(2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-1H-indol-3-yl)propan-1-ol hydrochloride; 
 (7) (±) 2-(5,6-dichloro-2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-1H-indol-3-yl)ethanol, citrate; 
 (8) (±) 2-(2-(4-morpholino-4-phenylcyclohex-1-enyl)-1H-indol-3-yl)ethanol, citrate; 
 (9) (±) 2-(4,6-dichloro-2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-1H-indol-3-yl)ethanol, citrate; 
 (10) (±) 2-(2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-5-fluoro-1H-indol-3-yl)ethanol, citrate; 
 (11) (±) 2-(2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-5-(pyridin-3-yl)-1H-indol-3-yl)ethanol, citrate; 
 (13) (±) 2-(2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-5-nitro-1H-indol-3-yl)ethanol, citrate; 
 (14) (±) 2-(2-(4-(benzo[b]thiophen-2-yl)-4-(dimethylamino)cyclohex-1-enyl)-1H-indol-3-yl)ethanol, citrate; 
 (15) (±) 2-(2-(4-(benzo[b]thiophen-2-yl)-4-(dimethylamino)cyclohex-1-enyl)-5-fluoro-1H-indol-3-yl)ethanol, citrate; 
 (16) (±) 2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-3-methyl-1H-indole, citrate; 
 (17) N,N-dimethyl-4-(3-methyl-1H-indol-2-yl)-1-phenylcyclohexanamine, citrate; 
 (18) N,N-dimethyl-4-(3-methyl-1H-indol-2-yl)-1-phenylcyclohexanamine, citrate; 
 (19) 2-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)isoindoline-1,3-dione, citrate; 
 (20) N-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)acetamide, citrate; 
 (21) N-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)acetamide, citrate; 
 (22) (±)-2-(4-benzyl-4-(dimethylamino)cyclohex-1-enyl)-3-methyl-1H-indole-5-carbonitrile; 
 (23) (±)-2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-3-methyl-1H-indole-5-carbonitrile; 
 (24) (±)-2-(4-(dimethylamino)-4-butylcyclohex-1-enyl)-3-methyl-5-trifluoromethyl-1H-indole; 
 (25) (±)-2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-3-methyl-5-trifluoromethyl-1H-indole, citrate; 
 (26) (±)-2-(4-(dimethylamino)-4-benzylcyclohex-1-enyl)-3-methyl-5-fluoro-1H-indole, citrate; 
 (27) (±)-2-(4-(dimethylamino)-4-butylcyclohex-1-enyl)-3-methyl-5-fluoro-1H-indole, citrate; 
 (28) (±)-2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-3-methyl-5-fluoro-1H-indole, citrate; 
 (29) (±)-2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-3-methyl-5-methoxy-1H-indole, citrate; 
 (30) (±)-2-(4-(dimethylamino)-4-benzylcyclohex-1-enyl)-3-methyl-1H-indole, citrate; 
 (31) (±)-2-(4-(dimethylamino)-4-butylcyclohex-1-enyl)-3-methyl-1H-indole, citrate; 
 (32) (±)-2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-3-methyl-1H-pyrrolo[2,3-b]pyridine, citrate; 
 (33) (±)-2-(4-(dimethylamino)-4-benzylcyclohex-1-enyl)-3-cyclopropyl-1H-indole hydrochloride; 
 (34) (±)-2-(4-(dimethylamino)-4-butylcyclohex-1-enyl)-3-cyclopropyl-1H-indole; 
 (35) (±)-2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-3-cyclopropyl-1H-indole; 
 (36) (±)-2-(4-(dimethylamino)-4-benzylcyclohex-1-enyl)-3-(cyclohexylmethyl)-1H-indole; 
 (37) (±)-2-(4-(dimethylamino)-4-benzylcyclohex-1-enyl)-3-benzyl-1H-indole hydrochloride; 
 (38) (±)-2-(4-(dimethylamino)-4-butylcyclohex-1-enyl)-3-(cyclohexylmethyl)-1H-indole hydrochloride; 
 (39) (±)-2-(4-(dimethylamino)-4-butylcyclohex-1-enyl)-3-benzyl-1H-indole; 
 (40) (±)-2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-3-(cyclohexylmethyl)-1H-indole hydrochloride; 
 (41) (±)-2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-3-benzyl-1H-indole hydrochloride; 
 (42) (±)-2-(4-(dimethylamino)-4-benzylcyclohex-1-enyl)-3-propyl-1H-indole; 
 (43) (±)-2-(4-(dimethylamino)-4-butylcyclohex-1-enyl)-3-propyl-1H-indole; 
 (44) (±)-2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-3-propyl-1H-indole; 
 (45) (±) 2-(4-(dimethylamino)-4-benzylcyclohex-1-enyl)-3-(2-(pyridin-4-yl)ethyl)-1H-indole; 
 (46) (±) 2-(4-(dimethylamino)-4-butylcyclohex-1-enyl)-3-(2-(pyridin-4-yl)ethyl)-1H-indole; 
 (47) (±) 2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-3-(2-(pyridin-4-yl)ethyl)-1H-indole; 
 (48) (±)-3-(2-(4-benzyl-4-(dimethylamino)cyclohex-1-enyl)-1H-indol-3-yl)propan-1-ol, citrate; 
 (49) (±)-3-(2-(4-butyl-4-(dimethylamino)cyclohex-1-enyl)-1H-indol-3-yl)propan-1-ol, citrate; 
 (51) (±) 2-(2-(2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-1H-indol-3-yl)ethyl)isoindoline-1,3-dione; 
 (52) (±) 2-(4-(dimethylamino)-4-benzylcyclohex-1-enyl)-3-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-5-fluoro-1H-indole; 
 (53) (±) 2-(4-(dimethylamino)-4-butylcyclohex-1-enyl)-3-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-5-fluoro-1H-indole; 
 (54) (±) 2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-3-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-5-fluoro-1H-indole; 
 (55) (±) 2-(4-(dimethylamino)-4-benzylcyclohex-1-enyl)-3-(2-(piperidin-1-yl)ethyl)-5-fluoro-1H-indole; 
 (56) (±) 2-(4-(dimethylamino)-4-butylcyclohex-1-enyl)-3-(2-(piperidin-1-yl)ethyl)-5-fluoro-1H-indole; 
 (57) (±) 2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-3-(2-(piperidin-1-yl)ethyl)-5-fluoro-1H-indole; 
 (58) (±) 2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-3-(2-(piperidin-1-yl)ethyl)-1H-indole, citrate; 
 (59) (±) 2-(4-(dimethylamino)-4-benzylcyclohex-1-enyl)-3-(2-(1H-1,2,3-triazol-1-yl)ethyl)-5-fluoro-1H-indole; 
 (60) (±) 2-(4-(dimethylamino)-4-butylcyclohex-1-enyl)-3-(2-(1H-1,2,3-triazol-1-yl)ethyl)-5-fluoro-1H-indole; 
 (61) (±) 2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-3-(2-(1H-1,2,3-triazol-1-yl)ethyl)-5-fluoro-1H-indole; 
 (62) N-(2-(2-(4-butyl-4-(dimethylamino)cyclohexyl)-1H-indol-3-yl)ethyl)-3,3-dimethylbutanamide, citrate; 
 (63) (±) N-(2-(2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-1H-indol-3-yl)ethyl)acetamide; 
 (64) (±) N-(2-(2-(4-butyl-4-(dimethylamino)cyclohex-1-enyl)-1H-indol-3-yl)ethyl)-3,3-dimethylbutanamide; 
 (65) (±)-2-(2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-5-fluoro-6-methoxy-1H-indol-3-yl)ethanol, citrate; 
 (66) (±)-2-(2-(4-benzyl-4-(4-methylpiperazin-1-yl)cyclohex-1-enyl)-5-fluoro-1H-indol-3-yl)ethanol; 
 (67) (±)-2-(5-fluoro-2-(4-phenyl-4-(pyrrolidin-1-yl)cyclohex-1-enyl)-1H-indol-3-yl)ethanol; 
 (68) 2-(4-benzyl-4-(dimethylamino)cyclohexyl)-3-methyl-1H-indole-5-carbonitrile, citrate; 
 (69) 2-(4-benzyl-4-(dimethylamino)cyclohexyl)-3-methyl-1H-indole-5-carbonitrile, citrate; 
 (70) 2-(4-butyl-4-(dimethylamino)cyclohexyl)-3-methyl-1H-indole-5-carbonitrile, citrate; 
 (71) 2-(4-butyl-4-(dimethylamino)cyclohexyl)-3-methyl-1H-indole-5-carbonitrile, citrate; 
 (72) 2-(4-(dimethylamino)-4-phenylcyclohexyl)-3-methyl-1H-indole-5-carbonitrile, citrate; 
 (73) 1-benzyl-N,N-dimethyl-4-(3-methyl-5-(trifluoromethyl)-1H-indol-2-yl)cyclohexanamine, citrate; 
 (74) 1-benzyl-N,N-dimethyl-4-(3-methyl-5-(trifluoromethyl)-1H-indol-2-yl)cyclohexanamine, citrate; 
 (75) 1-butyl-N,N-dimethyl-4-(3-methyl-5-(trifluoromethyl)-1H-indol-2-yl)cyclohexanamine, citrate; 
 (76) N,N-dimethyl-4-(3-methyl-5-(trifluoromethyl)-1H-indol-2-yl)-1-phenylcyclohexanamine, citrate; 
 (77) 1-benzyl-4-(5-fluoro-3-methyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine, citrate; 
 (78) 1-benzyl-4-(5-fluoro-3-methyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine, citrate; 
 (79) 1-butyl-4-(5-fluoro-3-methyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine hydrochloride; 
 (80) 4-(5-fluoro-3-methyl-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (81) 4-(5-fluoro-3-methyl-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (82) 4-(3-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-butyl-N,N-dimethylcyclohexanamine, citrate; 
 (83) 4-(3-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (84) 4-(3-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (85) 1-benzyl-4-(5-fluoro-3-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethylcyclohexanamine, citrate; 
 (86) 1-benzyl-4-(5-fluoro-3-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethylcyclohexanamine, citrate; 
 (87) 1-butyl-4-(5-fluoro-3-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethylcyclohexanamine, citrate; 
 (88) 1-butyl-4-(5-fluoro-3-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethylcyclohexanamine, citrate; 
 (89) 4-(5-fluoro-3-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (90) 4-(5-fluoro-3-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (91) 1-benzyl-4-(5-fluoro-3-(2-(piperidin-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethylcyclohexanamine, citrate; 
 (92) 1-benzyl-4-(5-fluoro-3-(2-(piperidin-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethylcyclohexanamine, citrate (2:3); 
 (93) 1-butyl-4-(5-fluoro-3-(2-(piperidin-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethylcyclohexanamine, citrate (4:3); 
 (94) 1-butyl-4-(5-fluoro-3-(2-(piperidin-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethylcyclohexanamine, citrate; 
 (95) 4-(5-fluoro-3-(2-(piperidin-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (96) 4-(5-fluoro-3-(2-(piperidin-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (97) 4-(3-(2-(1H-pyrazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-benzyl-N,N-dimethylcyclohexanamine, citrate (2:3); 
 (98) 4-(3-(2-(1H-pyrazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-benzyl-N,N-dimethylcyclohexanamine, citrate; 
 (99) 4-(3-(2-(1H-pyrazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-butyl-N,N-dimethylcyclohexanamine, citrate; 
 (100) 4-(3-(2-(1H-pyrazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-butyl-N,N-dimethylcyclohexanamine, citrate; 
 (101) 4-(3-(2-(1H-pyrazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (102) 4-(3-(2-(1H-pyrazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (103) 4-(3-(2-(1H-imidazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-benzyl-N,N-dimethylcyclohexanamine, citrate; 
 (104) 4-(3-(2-(1H-imidazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-benzyl-N,N-dimethylcyclohexanamine, citrate; 
 (105) 4-(3-(2-(1H-imidazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-butyl-N,N-dimethylcyclohexanamine, citrate (2:3); 
 (106) 4-(3-(2-(1H-imidazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-butyl-N,N-dimethylcyclohexanamine, citrate; 
 (107) 4-(3-(2-(1H-imidazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (108) 4-(3-(2-(1H-imidazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate (2:3); 
 (109) 4-(3-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-benzyl-N,N-dimethylcyclohexanamine, citrate (4:3); 
 (110) 4-(3-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-benzyl-N,N-dimethylcyclohexanamine, citrate (2:3); 
 (111) 4-(3-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-butyl-N,N-dimethylcyclohexanamine, citrate (2:3); 
 (112) 4-(3-(2-(1H-1,2,3-triazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-benzyl-N,N-dimethylcyclohexanamine, citrate (4:1); 
 (113) 4-(3-(2-(1H-1,2,3-triazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-benzyl-N,N-dimethylcyclohexanamine, citrate; 
 (114) 4-(3-(2-(1H-1,2,3-triazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-butyl-N,N-dimethylcyclohexanamine, citrate; 
 (115) 4-(3-(2-(1H-1,2,3-triazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-1-butyl-N,N-dimethylcyclohexanamine, citrate; 
 (116) 4-(3-(2-(1H-1,2,3-triazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (117) 4-(3-(2-(1H-1,2,3-triazol-1-yl)ethyl)-5-fluoro-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (118) 2-(4-(dimethylamino)-4-phenylcyclohexyl)-3-methyl-1H-indol-5-ol; 
 (119) 2-(4-(dimethylamino)-4-phenylcyclohexyl)-3-methyl-1H-indol-5-ol; 
 120) 1-benzyl-N,N-dimethyl-4-(3-methyl-5-(trifluoromethoxy)-1H-indol-2-yl)cyclohexanamine, citrate; 
 (121) 1-butyl-N,N-dimethyl-4-(3-methyl-5-(trifluoromethoxy)-1H-indol-2-yl)cyclohexanamine, citrate; 
 (122) 1-butyl-N,N-dimethyl-4-(3-methyl-5-(trifluoromethoxy)-1H-indol-2-yl)cyclohexanamine, citrate; 
 (123) N,N-dimethyl-4-(3-methyl-5-(trifluoromethoxy)-1H-indol-2-yl)-1-phenylcyclohexanamine, citrate; 
 (124) N,N-dimethyl-4-(3-methyl-5-(trifluoromethoxy)-1H-indol-2-yl)-1-phenylcyclohexanamine, citrate; 
 (125) 1-butyl-4-(5-methoxy-3-methyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine, citrate; 
 (126) 1-butyl-4-(5-methoxy-3-methyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine, citrate; 
 (127) 4-(5-methoxy-3-methyl-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (128) 4-(5-methoxy-3-methyl-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; (4:3); 
 (129) 1-benzyl-N,N-dimethyl-4-(3-methyl-1H-indol-2-yl)cyclohexanamine, citrate; 
 (130) 1-benzyl-N,N-dimethyl-4-(3-methyl-1H-indol-2-yl)cyclohexanamine, citrate; 
 (131) 1-butyl-N,N-dimethyl-4-(3-methyl-1H-indol-2-yl)cyclohexanamine, citrate; 
 (132) 1-butyl-N,N-dimethyl-4-(3-methyl-1H-indol-2-yl)cyclohexanamine, citrate; 
 (133) 1-benzyl-4-(3-cyclopropyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine, citrate; 
 (134) 1-benzyl-4-(3-cyclopropyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine, citrate; 
 (135) 1-butyl-4-(3-cyclopropyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine hydrochloride; 
 (136) 4-(3-cyclopropyl-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (137) methyl 2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)acetate, citrate; 
 (138) methyl 2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)acetate, citrate; 
 (139) 1-benzyl-4-(3-(cyclohexylmethyl)-1H-indol-2-yl)-N,N-dimethylcyclohexanamine, citrate; 
 (140) 1-benzyl-4-(3-(cyclohexylmethyl)-1H-indol-2-yl)-N,N-dimethylcyclohexanamine, citrate; 
 (141) 1-benzyl-4-(3-benzyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine, citrate; 
 (142) 1-benzyl-4-(3-benzyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine, citrate; 
 (143) 1-butyl-4-(3-(cyclohexylmethyl)-1H-indol-2-yl)-N,N-dimethylcyclohexanamine, citrate; 
 (144) 1-butyl-4-(3-(cyclohexylmethyl)-1H-indol-2-yl)-N,N-dimethylcyclohexanamine hydrochloride; 
 (145) 4-(3-benzyl-1H-indol-2-yl)-1-butyl-N,N-dimethylcyclohexanamine, citrate; 
 (146) 4-(3-benzyl-1H-indol-2-yl)-1-butyl-N,N-dimethylcyclohexanamine, citrate; 
 (147) 4-(3-(cyclohexylmethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (148) 4-(3-(cyclohexylmethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (149) 4-(3-benzyl-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (150) 4-(3-benzyl-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (151) N,N-dimethyl-1-phenyl-4-(3-(pyridin-2-ylmethyl)-1H-indol-2-yl)cyclohexanamine; 
 (152) N,N-dimethyl-1-phenyl-4-(3-(pyridin-2-ylmethyl)-1H-indol-2-yl)cyclohexanamine; 
 (153) 3-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)propanoic acid hydrochloride; 
 (156) 1-benzyl-N,N-dimethyl-4-(3-propyl-1H-indol-2-yl)cyclohexanamine, citrate; 
 (157) 1-butyl-N,N-dimethyl-4-(3-propyl-1H-indol-2-yl)cyclohexanamine hydrochloride; 
 (158) 1-butyl-N,N-dimethyl-4-(3-propyl-1H-indol-2-yl)cyclohexanamine, citrate; 
 (159) N,N-dimethyl-1-phenyl-4-(3-propyl-1H-indol-2-yl)cyclohexanamine, citrate; 
 (160) N,N-dimethyl-1-phenyl-4-(3-propyl-1H-indol-2-yl)cyclohexanamine, citrate; 
 (161) 1-benzyl-N,N-dimethyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate; 
 (162) 1-benzyl-N,N-dimethyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate; 
 (163) 1-butyl-N,N-dimethyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate; 
 (164) 1-butyl-N,N-dimethyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate; 
 (165) N,N-dimethyl-1-phenyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate (1:4); 
 (166) N,N-dimethyl-1-phenyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate; 
 (167) N,N-dimethyl-4-(3-(2-(1-methyl-1H-benzo[d]imidazol-2-yl)ethyl)-1H-indol-2-yl)-1-phenylcyclohexanamine, citrate; 
 (168) N,N-dimethyl-4-(3-(2-(1-methyl-1H-benzo[d]imidazol-2-yl)ethyl)-1H-indol-2-yl)-1-phenylcyclohexanamine, citrate; 
 (169) N,N-dimethyl-1-phenyl-4-(3-(2-(pyridin-2-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate; 
 (170) N,N-dimethyl-1-phenyl-4-(3-(2-(pyridin-2-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate (2:3); 
 (171) 4-(2-(4-benzyl-4-(dimethylamino)cyclohexyl)-1H-indol-3-yl)butanoic acid hydrochloride; 
 (172) 4-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)butanoic acid hydrochloride; 
 (173) 4-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)butan-1-ol hydrochloride; 
 (174) 4-(2-(4-benzyl-4-(dimethylamino)cyclohexyl)-1H-indol-3-yl)butyl acetate hydrochloride; 
 (175) 4-(2-(4-benzyl-4-(dimethylamino)cyclohexyl)-1H-indol-3-yl)butyl acetate hydrochloride; 
 (176) 4-(2-(4-butyl-4-(dimethylamino)cyclohexyl)-1H-indol-3-yl)butyl acetate hydrochloride; 
 (177) 4-(2-(4-butyl-4-(dimethylamino)cyclohexyl)-1H-indol-3-yl)butyl acetate hydrochloride; 
 (178) 4-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)butyl acetate hydrochloride; 
 (179) 4-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)butyl acetate hydrochloride; 
 (180) 3-(2-(4-benzyl-4-(dimethylamino)cyclohexyl)-1H-indol-3-yl)propan-1-ol, citrate; 
 (181) 3-(2-(4-butyl-4-(dimethylamino)cyclohexyl)-1H-indol-3-yl)propan-1-ol hydrochloride; 
 (182) 3-(2-(4-butyl-4-(dimethylamino)cyclohexyl)-1H-indol-3-yl)propan-1-ol hydrochloride; 
 (183) 3-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)propan-1-ol hydrochloride; 
 (184) 3-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)propan-1-ol hydrochloride; 
 (185) 3-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)propyl acetate hydrochloride; 
 (186) 3-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)propyl acetate hydrochloride; 
 (187) 1-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)pyrrolidine-2,5-dione; 
 (188) 1-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)pyrrolidine-2,5-dione; 
 (189) 4-(3-(2-(3,4-dihydroquinolin-1(2H)-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate (4:3); 
 (190) 4-(3-(2-(3,4-dihydroquinolin-1(2H)-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (191) methyl 1-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)-1H-1,2,3-triazole-4-carboxylate, citrate; 
 (192) methyl 1-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)-1H-1,2,3-triazole-4-carboxylate, citrate; 
 (193) 4-(3-(2-(isoindolin-2-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (194) 4-(3-(2-(isoindolin-2-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (195) 4-(3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (196) 4-(3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate (2:3); 
 (197) N,N-dimethyl-1-phenyl-4-(3-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate; 
 (198) N,N-dimethyl-1-phenyl-4-(3-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate; 
 (199) N,N-dimethyl-1-phenyl-4-(3-(2-(piperidin-1-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate; 
 (200) N,N-dimethyl-4-(3-(2-(4-methylpiperazin-1-yl)ethyl)-1H-indol-2-yl)-1-phenylcyclohexanamine, citrate; 
 (201) N,N-dimethyl-4-(3-(2-morpholinoethyl)-1H-indol-2-yl)-1-phenylcyclohexanamine, citrate; 
 (202) N,N-dimethyl-4-(3-(2-morpholinoethyl)-1H-indol-2-yl)-1-phenylcyclohexanamine, citrate; 
 (203) 4-(3-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (204) 4-(3-(2-(1H-benzo[d]imidazol-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (205) 4-(3-(2-(1H-imidazol-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (206) 4-(3-(2-(1H-imidazol-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (207) 4-(3-(2-(1H-1,2,4-triazol-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (208) 4-(3-(2-(1H-1,2,4-triazol-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (209) N,N-dimethyl-1-phenyl-4-(3-(2-(thiazolidin-3-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate; 
 (210) N,N-dimethyl-1-phenyl-4-(3-(2-(thiazolidin-3-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate; 
 (211) N,N-dimethyl-4-(3-(2-(5-methyl-2H-tetrazol-2-yl)ethyl)-1H-indol-2-yl)-1-phenylcyclohexanamine, citrate; 
 (212) N,N-dimethyl-4-(3-(2-(5-methyl-2H-tetrazol-2-yl)ethyl)-1H-indol-2-yl)-1-phenylcyclohexanamine, citrate; 
 (213) 4-(3-(2-(1H-pyrazol-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (214) 4-(3-(2-(1H-pyrazol-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (215) 4-(3-(2-(1H-1,2,3-triazol-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (216) 4-(3-(2-(1H-1,2,3-triazol-1-yl)ethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (217) N,N-dimethyl-4-(3-(2-(5-methyl-1H-tetrazol-1-yl)ethyl)-1H-indol-2-yl)-1-phenylcyclohexanamine, citrate; 
 (218) N,N-dimethyl-4-(3-(2-(5-methyl-1H-tetrazol-1-yl)ethyl)-1H-indol-2-yl)-1-phenylcyclohexanamine, citrate; 
 (219) 2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethanol; 
 (220) 2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl acetate; 
 (221) N,N-dimethyl-4-(3-methyl-1H-pyrrolo[3,2-c]pyridin-2-yl)-1-phenylcyclohexanamine, citrate; 
 (222) N,N-dimethyl-4-(3-methyl-1H-pyrrolo[3,2-c]pyridin-2-yl)-1-phenylcyclohexanamine, citrate; 
 (223) N,N-dimethyl-4-(3-methyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-1-phenylcyclohexanamine, citrate; 
 (224) N,N-dimethyl-4-(3-methyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-1-phenylcyclohexanamine, citrate; 
 (225) N,N-dimethyl-4-(3-methylbenzofuran-2-yl)-1-phenylcyclohexanamine, citrate; 
 (226) N,N-dimethyl-4-(3-methylbenzofuran-2-yl)-1-phenylcyclohexanamine, citrate; 
 (227) 4-(1H-indol-3-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (228) (±)-3-(4-(dimethylamino)-4-benzylcyclohex-1-enyl)-1H-pyrrolo[2,3-b]pyridine; 
 (229) (±)-3-(4-(dimethylamino)-4-butylcyclohex-1-enyl)-1H-pyrrolo[2,3-b]pyridine; 
 (230) (±)-3-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-1H-pyrrolo[2,3-b]pyridine, citrate; 
 (231) (±)-4-(1H-indol-3-yl)-N,N-dimethyl-1-phenylcyclohex-3-enamine, citrate; 
 (232) (±)-4-(1H-indol-3-yl)-N,N-dimethyl-1-phenylcyclohex-3-enamine; 
 (233) (±)-2-(3-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)benzo[b]thiophen-2-yl)ethanol hydrochloride; 
 (234) (±)-2-(3-(4-(dimethylamino)-4-(pyridin-2-yl)cyclohex-1-enyl)benzo[b]thiophen-2-yl)ethanol hydrochloride; 
 (235) 4-(1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (236) 4-(1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine, citrate; 
 (237) 1-benzyl-N,N-dimethyl-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)cyclohexanamine hydrochloride; 
 (238) 1-butyl-N,N-dimethyl-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)cyclohexanamine hydrochloride; 
 (239) (±)-4-(benzofuran-2-yl)-1-benzyl-N,N-dimethylcyclohex-3-enamine hydrochloride; 
 (240) (±)-N,N-dimethyl-4-(3-methylbenzofuran-2-yl)-1-phenylcyclohex-3-enamine, citrate; 
 (241) (±)-2-(2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)benzofuran-3-yl)ethanethiol, citrate; 
 (242) (±)-N,N-dimethyl-4-(3-methylbenzo[b]thiophen-2-yl)-1-phenylcyclohex-3-enamine, citrate; 
 (243) N,N-dimethyl-4-(3-methylbenzo[b]thiophen-2-yl)-1-phenylcyclohexanamine, citrate; 
 (244) N,N-dimethyl-1-phenyl-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)cyclohexanamine, citrate; 
 (246) 1-(dimethylamino)-3-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-3-methyl-1H-indol-1-yl)propan-2-ol; 
 (247) N,N-dimethyl-4-(3-methyl-1-(oxiran-2-ylmethyl)-1H-indol-2-yl)-1-phenylcyclohexanamine; 
 (248) 4-(1,3-dimethyl-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine; 
 (249) 2-(4-butyl-4-(dimethylamino)cyclohexyl)-3-methyl-1H-indol-5-ol, citrate; 
 (250) 2-(4-butyl-4-(dimethylamino)cyclohexyl)-3-methyl-1H-indol-5-ol, citrate; 
 (251) (±)-2-(4-(dimethylamino)-4-(thiophen-2-yl)-cyclohex-1-enyl)-3-(2-(pyridin-4-yl)ethyl)-1H-indole; 
 (252) (±)-2-(4-(dimethylamino)-4-(3-fluorophenyl)-cyclohex-1-enyl)-3-(2-(pyridin-4-yl)ethyl)-1H-indole; 
 (253) (±)-2-(4-butyl-4-(pyrrolidin-1-yl)cyclohex-1-enyl)-3-(2-(pyridin-4-yl)ethyl)-1H-indole; 
 (254) (±)-2-(4-(methylamino)-4-phenylcyclohex-1-enyl)-3-(2-(pyridin-4-yl)ethyl)-1H-indole; 
 (255) (±)-2-(4-(dimethylamino)-4-(thiophen-2-yl)-cyclohex-1-enyl)-3-methyl-1H-indole, citrate; 
 (256) N,N-dimethyl-4-(3-methyl-1H-indol-2-yl)-1-(thiophen-2-yl)cyclohexanamine, citrate; 
 (257) N,N-dimethyl-4-(3-methyl-1H-indol-2-yl)-1-(thiophen-2-yl)cyclohexanamine, citrate; 
 (258) 2-(4-butyl-4-(pyrrolidin-1-yl)cyclohex-1-enyl)-3-methyl-1H-indole; 
 (259) N-methyl-4-(3-methyl-1H-indol-2-yl)-1-phenylcyclohexanamine hydrobromide; 
 (260) N-methyl-4-(3-methyl-1H-indol-2-yl)-1-phenylcyclohexanamine, citrate; 
 (261) 1-(3-fluorophenyl)-N,N-dimethyl-4-(3-methyl-1H-indol-2-yl)cyclohexanamine, citrate; 
 (262) 1-(3-fluorophenyl)-N,N-dimethyl-4-(3-methyl-1H-indol-2-yl)cyclohexanamine, citrate; 
 (263) (±)-2-(4-(dimethylamino)-4-(3-fluorophenyl)-cyclohex-1-enyl)-3-methyl-1H-indole; 
 (264) 2-(4-benzyl-4-(dimethylamino)cyclohexyl)-3-methyl-1H-indol-5-ol, citrate; 
 (265) 2-(4-benzyl-4-(dimethylamino)cyclohexyl)-3-methyl-1H-indol-5-ol, citrate; 
 (266) 2-(4-butyl-4-(pyrrolidin-1-yl)cyclohexyl)-3-(2-(pyridin-4-yl)ethyl)-1H-indole, citrate; 
 (267) 2-(4-butyl-4-(pyrrolidin-1-yl)cyclohexyl)-3-(2-(pyridin-4-yl)ethyl)-1H-indole, citrate; 
 (268) 2-(4-(azetidin-1-yl)-4-phenylcyclohexyl)-3-methyl-1H-indole, citrate; 
 (269) 2-(4-(azetidin-1-yl)-4-phenylcyclohexyl)-3-methyl-1H-indole, citrate; 
 (270) 2-(4-(azetidin-1-yl)-4-phenylcyclohexyl)-3-(2-(pyridin-4-yl)ethyl)-1H-indole hydrochloride; 
 (271) 2-(4-(azetidin-1-yl)-4-phenylcyclohexyl)-3-(2-(pyridin-4-yl)ethyl)-1H-indole hydrochloride; 
 (272) 2-(4-butyl-4-(pyrrolidin-1-yl)cyclohexyl)-3-methyl-1H-indole, citrate; 
 (273) 3-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)propan-1-ol, citrate; 
 (274) 1-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-3-methyl-1H-indol-1-yl)-3-(methylamino)propan-2-ol, citrate; 
 (275) 1-benzyl-3-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)urea, citrate; 
 (276) 1-benzyl-3-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)urea, citrate; 
 (277) 1-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)-3-phenylurea, citrate; 
 (278) 1-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)-3-phenylurea, citrate; 
 (279) 1-cyclopentyl-3-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)urea, citrate; 
 (280) 1-cyclopentyl-3-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)urea, citrate; 
 (281) N-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)-cyclopentanesulfonamide, citrate; 
 (282) N-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)cyclopentanesulfonamide, citrate; 
 (283) N-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)benzenesulfonamide, citrate; 
 (284) N-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)thiophene-2-sulfonamide, citrate; 
 (285) N-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)thiophene-2-sulfonamide, citrate; 
 (286) N-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)nicotinamide, citrate; 
 (287) N-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)nicotinamide, citrate; 
 (288) N-(2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethyl)benzamide, citrate; 
 (289) 1-(3-fluorophenyl)-N,N-dimethyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)cyclohexanamine; 
 (290) 1-(3-fluorophenyl)-N,N-dimethyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate; 
 (291) N-methyl-1-phenyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate; 
 (292) N-methyl-1-phenyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)cyclohexanamine, citrate; 
 (293) 2-(4-butyl-4-(pyrrolidin-1-yl)cyclohexyl)-3-methyl-1H-indole, citrate; 
 (294) N,N-dimethyl-1-phenyl-4-(1-(phenylsulfonyl)-1H-indol-2-yl)cyclohexanamine; 
 (295) N,N-dimethyl-1-phenyl-4-(1-(phenylsulfonyl)-1H-indol-2-yl)cyclohexanamine; 
 (296) N,N-dimethyl-4-(3-methyl-1-(oxiran-2-ylmethyl)-1H-indol-2-yl)-1-phenylcyclohex-3-enamine; 
 (297) N,N-dimethyl-4-(3-methyl-1-(oxiran-2-ylmethyl)-1H-indol-2-yl)-1-phenylcyclohexanamine, citrate; 
 (298) 1-(dimethylamino)-3-(2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-3-methyl-1H-indol-1-yl)propan-2-ol, citrate; 
 (299) 1-(dimethylamino)-3-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-3-methyl-1H-indol-1-yl)propan-2-ol, citrate; 
 (300) 2-(3-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-1H-indol-1-yl)ethanol hydrochloride; 
 (301) (±) 3-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-(1-(phenylsulfonyl)-1H-indole) hydrochloride; 
 (302) 1-benzyl-N,N-dimethyl-4-(1-methyl-1H-indol-2-yl)cyclohex-3-enamine; hydrochloride; 
 (303) N,N-dimethyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)-1-(thiophen-2-yl)cyclohexanamine hydrochloride; 
 (304) N,N-dimethyl-4-(3-(2-(pyridin-4-yl)ethyl)-1H-indol-2-yl)-1-(thiophen-2-yl)cyclohexanamine hydrochloride; 
 (305) N-methyl-4-(3-methyl-1H-indol-2-yl)-1-(4-methylthiazol-2-yl)cyclohexanamine; 
 (306) N-methyl-4-(3-methyl-1H-indol-2-yl)-1-(4-methylthiazol-2-yl)cyclohexanamine; and 
 (307) 2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethanol;
 in the form of the racemate; of the enantiomers, diastereomers, mixtures of the enantiomers or diastereomers or of an individual enantiomer or diastereomer; of the bases and/or salts of physiologically acceptable acids. 
 
 
     
     
       12. Process for the preparation of substituted heteroaryl derivatives of the formula Ic 
       
         
           
           
               
               
           
         
         comprising reacting ketones of the formula B with heteroaromatics of the formula A in organic solvents or solvent mixtures with the addition of an organic or inorganic acid, or without a solvent in an organic or inorganic acid or acid mixtures at temperatures of between 0° C. and 150° C., optionally using microwave irradiation, and then reacting with the addition of an organic or inorganic reducing agent at temperatures of between 0° C. and 150° C., optionally using microwave irradiation. 
       
     
     
       13. Process for the preparation of substituted heteroaryl derivatives of the general formula Id or Ie 
       
         
           
           
               
               
           
         
         comprising reacting heteroaromatics of the formula A or A′ with cyclohexanones of the formula B in organic solvents or solvent mixtures with the addition of an organic or inorganic acid at temperatures of between 0° C. and 150° C., optionally using microwave irradiation; 
         or reacting heteroaromatics of the formula A or A′ with cyclohexanones of the formula B with the addition of a base in an organic solvent at temperatures of between 20 and 100° C. 
       
     
     
       14. Process for the preparation of substituted heteroaryl derivatives of the formulae Ic or If 
       
         
           
           
               
               
           
         
         comprising reducing compounds Id or Ie by means of hydrogen in the form of HBr/glacial acetic acid/Sn or HCl/Sn (nascent hydrogen) or H 2  in the presence of a metal catalyst in a suitable solvent or solvent mixture at temperatures of between 0° C. and 150° C. 
       
     
     
       15. A pharmaceutical composition comprising at least one substituted heteroaryl derivative according  claim 1 , optionally in the form of its racemate, of the pure stereoisomers, of a mixture of multiple stereoisomers in any desired mixture ratio; in the form of its acids or of its bases or in the form of its salts; and optionally containing suitable additives and/or auxiliary substances and/or optionally further active compounds. 
     
     
       16. A method of treating pain, selected from the group consisting of acute pain, chronic pain, and neuropathic pain, in a patient in need of such treatment, said method comprising administering to said patient an effective amount therefor of a substituted heteroaryl derivative according to  claim 1 , optionally in the form of its racemate, of the pure stereoisomers, of a mixture of multiple stereoisomers in any desired mixture ratio; in the form of its acids or of its bases or in the form of its salts. 
     
     
       17. Substituted heteroaryl derivatives according to  claim 1 , which has the formula: 
       
         
           
           
               
               
           
         
         wherein 
            represents a single bond or a double bond, 
         A 1  represents N or CR 7 ; 
         A 3  represents N or CR 9 ; and 
         W represents O, S or NR 4 ; 
       
       with the proviso that if W represents O or S, then A 1  represents CR 7  and A 3  represents CR 9 ;
 B represents (CH 2 ) 1-4 —R 21 , wherein R 21  represents H, OH, SH, COOC 1-6 -alkyl, COOH, OC(═O)C 1-6 -alkyl, NH 2 , NHC(═O)C 1-6 -alkyl; or C 3-8 -cycloalkyl, aryl or heteroaryl, in each case unsubstituted or mono- or polysubstituted; 
 R 1  and R 2  independently of one another represent H; C 1-5 -alkyl, saturated, branched or unbranched, unsubstituted; 
 or the radicals R 1  and R 2  together form a ring and denote CH 2 CH 2 OCH 2 CH 2 , CH 2 CH 2 NR 11 CH 2 CH 2  or (CH 2 ) 3-6 ;
 wherein R 11  denotes H; C 1-5 -alkyl, saturated, branched or unbranched, unsubstituted; 
 
 R 3  represents C 1-8 -alkyl, in each case saturated or unsaturated, branched or unbranched, mono- or polysubstituted or unsubstituted; C 3-8 -cycloalkyl, in each case mono- or polysubstituted or unsubstituted; aryl or heteroaryl, in each case unsubstituted or mono- or polysubstituted; aryl, heteroaryl or C 3-8 -cycloalkyl, bonded via C 1-3 -alkyl group and in each case unsubstituted or mono- or polysubstituted; 
 R 4  represents H; C 1-5 -alkyl, saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted; or cycloalkyl, bonded via a C 1-3 -alkyl group and in each case mono- or polysubstituted or unsubstituted; COR 12 ; SO 2 R 12 ;
 wherein R 12  denotes H; C 1-5 -alkyl, saturated, branched or unbranched, unsubstituted; or aryl, mono- or polysubstituted or unsubstituted; 
 
 R 7  and R 9  independently of one another represent H, methyl, ethyl, propyl, butyl, pyridyl, O-benzyl, F, Cl, Br, I, CN, CF 3 , OCF 3 , OH, OCH 3 , NH 2 , COOH, COOCH 3 , NHCH 3  or N(CH 3 ) 2  or NO 2 ; 
 in the form of the racemate; of the enantiomers, diastereomers, mixtures of the enantiomers or diastereomers or of an individual enantiomer or diastereomer; of the bases and/or salts of physiologically acceptable acids.